Luxury Caribbean Cruises

Take a look through our impressive Caribbean cruise deals and take your pick. Or if you don’t see anything that you like then make sure you give our award-winning Cruise Concierge team a call and they will work hard to create your perfect getaway.

Find Out More About Cruising to the Caribbean

Showing 30 out of 1449 cruises
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Fly Cruise From:
Was £12594pp Now: £12090pp

Discover the Yachting Islands of the Caribbean

San Juan (Puerto Rico) | Vieques | Saint John Island | Great Harbour | Philipsburg | Gustavia | Little Bay | Saint John's | Basseterre | Îles des Saintes | Deshaies | Gustavia | Virgin Gorda | Norman Island | San Juan (Puerto Rico)

  • 10 Mar 2029
  • 14 Nights
Fly Cruise From:
Was £12594pp Now: £12090pp
View cruise Enquire Enquire
REF: EMERALD2J17100329-1
Fly Cruise From:
Was £5177pp Now: £4969pp

Grenadines & Windwards yachting

Bridgetown | Speightstown | Saint Vincent | Kingstown | Port Elizabeth | Mayreau Island | Union Island | Mayreau Island | Union Island | Tobago Cays | Bridgetown

  • 12 Mar 2029
  • 7 Nights
Fly Cruise From:
Was £5177pp Now: £4969pp
View cruise Enquire Enquire
REF: EMERALDE01J120329-1
Fly Cruise From:
Was £6254pp Now: £5941pp

Basslines & Beaches

Miami | Samaná | Charlotte Amalie | Gustavia | Saint John's | Tortola | Miami

  • 12 Mar 2029
  • 10 Nights
Book now with a 7.5% low deposit* - Ends 8th July
Fly Cruise From:
Was £6254pp Now: £5941pp
View cruise Enquire Enquire
REF: REGENTGRA290312
Fly Cruise From:
Was £3809pp Now: £3599pp

Maya Magic & Island Sun

Miami | Progreso | Cozumel | Harvest Caye | Miami

  • 13 Mar 2029
  • 7 Nights
Choose between FREE Wine, Beer & Champagne by the glass with lunch and dinner OR shore excursion credit
Fly Cruise From:
Was £3809pp Now: £3599pp
View cruise Enquire Enquire
REF: OCEANIAVIS290313
Fly Cruise From:
Was £6559pp Now: £6198pp

Antillean Azure Panorama

Miami | Georgetown | Ocho Rios | Oranjestad | Willemstad | Kralendijk | Saint George's | Fort-de-France | Philipsburg | Miami

  • 15 Mar 2029
  • 14 Nights
Choose between FREE Wine, Beer & Champagne by the glass with lunch and dinner OR shore excursion credit
Fly Cruise From:
Was £6559pp Now: £6198pp
View cruise Enquire Enquire
REF: OCEANIASON290315
Fly Cruise From:
Was £5276pp Now: £5064pp

Cruising the Leeward Islands

Philipsburg | Basseterre | Anguilla | Virgin Gorda | Gustavia | Philipsburg

  • 17 Mar 2029
  • 7 Nights
Fly Cruise From:
Was £5276pp Now: £5064pp
View cruise Enquire Enquire
REF: EMERALDE08J170329-1
Fly Cruise From:
Was £5531pp Now: £5309pp

Caribbean Yachting Discovery

Saint John's | Basseterre | Îles des Saintes | Deshaies | Gustavia | Virgin Gorda | Norman Island | San Juan (Puerto Rico)

  • 17 Mar 2029
  • 7 Nights
Fly Cruise From:
Was £5531pp Now: £5309pp
View cruise Enquire Enquire
REF: EMERALDE18J170329-2
Fly Cruise From:
Was £11820pp Now: £11347pp

Discover the Pearls of the Caribbean

Philipsburg | Basseterre | Anguilla | Virgin Gorda | Gustavia | Philipsburg | Virgin Gorda | Gustavia | Charlestown | Saint John's | Îles des Saintes | Soufrière | Bridgetown

  • 17 Mar 2029
  • 14 Nights
Fly Cruise From:
Was £11820pp Now: £11347pp
View cruise Enquire Enquire
REF: EMERALD2J02170329-1
Fly Cruise From:
Was £12594pp Now: £12090pp

Discover the Yachting Islands of the Caribbean

Saint John's | Basseterre | Îles des Saintes | Deshaies | Gustavia | Virgin Gorda | Norman Island | San Juan (Puerto Rico) | Vieques | Saint John Island | Great Harbour | Philipsburg | Gustavia | Little Bay | Saint John's

  • 17 Mar 2029
  • 14 Nights
Fly Cruise From:
Was £12594pp Now: £12090pp
View cruise Enquire Enquire
REF: EMERALD2J17170329-2
Fly Cruise From:
Was £5177pp Now: £4969pp

Grenadines & Windwards yachting

Bridgetown | Speightstown | Saint Vincent | Kingstown | Port Elizabeth | Mayreau Island | Union Island | Mayreau Island | Union Island | Tobago Cays | Bridgetown

  • 19 Mar 2029
  • 7 Nights
Fly Cruise From:
Was £5177pp Now: £4969pp
View cruise Enquire Enquire
REF: EMERALDE01J190329-1
Fly Cruise From:
Was £43990pp Now: £42230pp

Longitudinal World Cruise VII

Ushuaia | Antarctic Experience | Antarctica | Antarctic Experience | Antarctica | Ushuaia | Garibaldi Fjord | Chilean Fjords | Punta Arenas | Chilean Fjords | Puerto Chacabuco | Valparaiso | Iquique | Callao | Fuerte Amador | Port Antonio | Inagua | San Salvador Island | New York | Halifax | Sydney | Bonne Bay Canada | Havre-Saint-Pierre | Tadoussac | Quebec City | Trois-Rivieres (Three Rivers) | Toronto | Port Colborne | Point Pelee National Park | Detroit | Alpena | Mackinac Island | Milwaukee

  • 20 Mar 2029
  • 61 Nights
Receive a FREE Silver Spirits Drinks Package on ALL Ocean and Expedition voyages
Fly Cruise From:
Was £43990pp Now: £42230pp
View cruise Enquire Enquire
REF: VIKINGXOC290320D
Fly Cruise From:
Was £5139pp Now: £4856pp

Tropical Peaks & Palms

Miami | San Juan (Puerto Rico) | Saint John's | Castries | Bridgetown | Roseau | Tortola | Miami

  • 20 Mar 2029
  • 11 Nights
Choose between FREE Wine, Beer & Champagne by the glass with lunch and dinner OR shore excursion credit
Fly Cruise From:
Was £5139pp Now: £4856pp
View cruise Enquire Enquire
REF: OCEANIAVIS290320
Fly Cruise From:
Was £6285pp Now: £5970pp

The Sea To Seville

Miami | Nassau | Ponta Delgada | Funchal | Cádiz | Barcelona

  • 22 Mar 2029
  • 14 Nights
Launch Offer - Includes savings of up to 10% - On selected suite grades
Book now with a 7.5% low deposit* - Ends 8th July
Fly Cruise From:
Was £6285pp Now: £5970pp
View cruise Enquire Enquire
REF: REGENTGRA290322
Fly Cruise From:
Was £11611pp Now: £11030pp

Crossing To Spring

Miami | Nassau | Ponta Delgada | Funchal | Cádiz | Barcelona | Palamós | Sète | Monaco | Portofino | Livorno | Civitavecchia

  • 22 Mar 2029
  • 21 Nights
Book now with a 7.5% low deposit* - Ends 8th July
Fly Cruise From:
Was £11611pp Now: £11030pp
View cruise Enquire Enquire
REF: REGENTGRA290322A
Fly Cruise From:
Was £5176pp Now: £4968pp

Eastern Caribbean with St. Barths

Philipsburg | Virgin Gorda | Gustavia | Charlestown | Saint John's | Îles des Saintes | Soufrière | Bridgetown

  • 24 Mar 2029
  • 7 Nights
Fly Cruise From:
Was £5176pp Now: £4968pp
View cruise Enquire Enquire
REF: EMERALDE02J240329-1
Fly Cruise From:
Was £5631pp Now: £5405pp

Caribbean Yachting Hideaways

San Juan (Puerto Rico) | Vieques | Saint John Island | Great Harbour | Philipsburg | Gustavia | Little Bay | Saint John's

  • 24 Mar 2029
  • 7 Nights
Fly Cruise From:
Was £5631pp Now: £5405pp
View cruise Enquire Enquire
REF: EMERALDE17J240329-1
Fly Cruise From:
Was £12594pp Now: £12090pp

Discover the Yachting Islands of the Caribbean

San Juan (Puerto Rico) | Vieques | Saint John Island | Great Harbour | Philipsburg | Gustavia | Little Bay | Saint John's | Basseterre | Îles des Saintes | Deshaies | Gustavia | Virgin Gorda | Norman Island | San Juan (Puerto Rico)

  • 24 Mar 2029
  • 14 Nights
Fly Cruise From:
Was £12594pp Now: £12090pp
View cruise Enquire Enquire
REF: EMERALD2J17240329-1
Fly Cruise From:
Was £5177pp Now: £4969pp

Grenadines & Windwards yachting

Bridgetown | Speightstown | Saint Vincent | Kingstown | Port Elizabeth | Mayreau Island | Union Island | Mayreau Island | Union Island | Tobago Cays | Bridgetown

  • 26 Mar 2029
  • 7 Nights
Fly Cruise From:
Was £5177pp Now: £4969pp
View cruise Enquire Enquire
REF: EMERALDE01J260329-1
Fly Cruise From:
Was £5159pp Now: £4875pp

Tropics To Iberia Crossing

Miami | Nassau | Ponta Delgada | Funchal | Málaga | Barcelona

  • 29 Mar 2029
  • 14 Nights
Choose between FREE Wine, Beer & Champagne by the glass with lunch and dinner OR shore excursion credit
Fly Cruise From:
Was £5159pp Now: £4875pp
View cruise Enquire Enquire
REF: OCEANIASON290329
Fly Cruise From:
Was £8949pp Now: £8456pp

Azores To Ancient Shores

Miami | Nassau | Ponta Delgada | Funchal | Málaga | Barcelona | Palamós | Marseille | Livorno | Civitavecchia | Salerno | Messina | Valletta | Mykonos | Piraeus

  • 29 Mar 2029
  • 24 Nights
Choose between FREE Wine, Beer & Champagne by the glass with lunch and dinner OR shore excursion credit
Fly Cruise From:
Was £8949pp Now: £8456pp
View cruise Enquire Enquire
REF: OCEANIASON290329A
Fly Cruise From:
Was £5179pp Now: £4971pp

Eastern Caribbean with St. Barths

Bridgetown | Soufrière | Îles des Saintes | Saint John's | Charlestown | Gustavia | Virgin Gorda | Philipsburg

  • 31 Mar 2029
  • 7 Nights
Fly Cruise From:
Was £5179pp Now: £4971pp
View cruise Enquire Enquire
REF: EMERALDE02J310329-2
Fly Cruise From:
Was £5531pp Now: £5309pp

Caribbean Yachting Discovery

Saint John's | Basseterre | Îles des Saintes | Deshaies | Gustavia | Virgin Gorda | Norman Island | San Juan (Puerto Rico)

  • 31 Mar 2029
  • 7 Nights
Fly Cruise From:
Was £5531pp Now: £5309pp
View cruise Enquire Enquire
REF: EMERALDE18J310329-2
Fly Cruise From:
Was £11678pp Now: £11210pp

Discover the Pearls of the Caribbean

Bridgetown | Soufrière | Îles des Saintes | Saint John's | Charlestown | Gustavia | Virgin Gorda | Philipsburg | Basseterre | Anguilla | Virgin Gorda | Gustavia | Philipsburg

  • 31 Mar 2029
  • 14 Nights
Fly Cruise From:
Was £11678pp Now: £11210pp
View cruise Enquire Enquire
REF: EMERALD2J02310329-2
Fly Cruise From:
Was £12404pp Now: £11907pp

Discover the Yachting Islands of the Caribbean

Saint John's | Basseterre | Îles des Saintes | Deshaies | Gustavia | Virgin Gorda | Norman Island | San Juan (Puerto Rico) | Vieques | Saint John Island | Great Harbour | Philipsburg | Gustavia | Little Bay | Saint John's

  • 31 Mar 2029
  • 14 Nights
Fly Cruise From:
Was £12404pp Now: £11907pp
View cruise Enquire Enquire
REF: EMERALD2J17310329-2
Fly Cruise From:
Was £4549pp Now: £4298pp

Springtime Sea Serenade

Miami | Nassau | Ponta Delgada | Lisbon | Southampton

  • 31 Mar 2029
  • 14 Nights
Choose between FREE Wine, Beer & Champagne by the glass with lunch and dinner OR shore excursion credit
Fly Cruise From:
Was £4549pp Now: £4298pp
View cruise Enquire Enquire
REF: OCEANIAVIS290331
Fly Cruise From:
Was £7989pp Now: £7549pp

Atlantic & Highland Jewels

Miami | Nassau | Ponta Delgada | Lisbon | Southampton | Le Havre | Zeebrugge | Newhaven/Edinburgh | Invergordon | Kirkwall | Lerwick | Bergen | Amsterdam

  • 31 Mar 2029
  • 24 Nights
Choose between FREE Wine, Beer & Champagne by the glass with lunch and dinner OR shore excursion credit
Fly Cruise From:
Was £7989pp Now: £7549pp
View cruise Enquire Enquire
REF: OCEANIAVIS290331A
Fly Cruise From:
Was £5053pp Now: £4850pp

Grenadines & Windwards yachting

Bridgetown | Speightstown | Saint Vincent | Kingstown | Port Elizabeth | Mayreau Island | Union Island | Mayreau Island | Union Island | Tobago Cays | Bridgetown

  • 02 Apr 2029
  • 7 Nights
Fly Cruise From:
Was £5053pp Now: £4850pp
View cruise Enquire Enquire
REF: EMERALDE01J020429-1
Fly Cruise From:
Was £5262pp Now: £5051pp

Cruising the Leeward Islands

Philipsburg | Basseterre | Anguilla | Virgin Gorda | Gustavia | Philipsburg

  • 07 Apr 2029
  • 7 Nights
Fly Cruise From:
Was £5262pp Now: £5051pp
View cruise Enquire Enquire
REF: EMERALDE08J070429-1
Fly Cruise From:
Was £5465pp Now: £5246pp

Caribbean Yachting Hideaways

San Juan (Puerto Rico) | Vieques | Saint John Island | Great Harbour | Philipsburg | Gustavia | Little Bay | Saint John's

  • 07 Apr 2029
  • 7 Nights
Fly Cruise From:
Was £5465pp Now: £5246pp
View cruise Enquire Enquire
REF: EMERALDE17J070429-1
Fly Cruise From:
Was £5053pp Now: £4850pp

Grenadines & Windwards yachting

Bridgetown | Speightstown | Saint Vincent | Kingstown | Port Elizabeth | Mayreau Island | Union Island | Mayreau Island | Union Island | Tobago Cays | Bridgetown

  • 09 Apr 2029
  • 7 Nights
Fly Cruise From:
Was £5053pp Now: £4850pp
View cruise Enquire Enquire
REF: EMERALDE01J090429-1

Prices are subject to change and availability. Prices may vary depending on the airport selected. Promotions are only applicable to select cabin grades, please call for details.

Caribbean Cruise Deals

Choosing your ideal itinerary can be tricky as this is such a diverse region to explore, but with our equally diverse Caribbean cruise deals, you needn’t worry. Here you will find 7 to 14-day sailings visiting each region, or you can embark on a longer adventure and visit East, West and South, all in one cruise holiday. The choice is completely up to you.

Top 5 places to discover in the Caribbean

  • San Juan - Puerto Rico - Whether you fancy a sunshine-filled beach holiday or want to explore a capital bursting with culture, San Juan offers both.
  • Bridgetown - Barbados - As the capital of Barbados there are plenty of things to do here.
  • Ocho Rios - Jamaica - Your stresses will truly melt away when you arrive in this laid-back port of call.
  • Oranjestad - Aruba - This is a great place to see Dutch colonial architecture, with brightly coloured buildings scattered throughout the city.
  • Castries - St. Lucia - Quite possibly one of our favourite islands in the Caribbean, St. Lucia has a beautiful capital city with plenty to see and do.

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